Triethylamine → Methyl 2-{[(5-methylpyridin-3-yl)amino]sulfonyl}benzoate

HRID 252208

Reaktionsgleichung

Reaktionsgleichung von HRID 252208
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[S:17]([C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23])(=[O:19])=[O:18]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][S:17]([C:20]2[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=2[C:22]([O:24][CH3:25])=[O:23])(=[O:19])=[O:18])[CH:5]=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 27628943-Amino-5-methylpyridine

Produkt 1

HCID 58924073Methyl 2-{[(5-methylpyridin-3-yl)amino]sulfonyl}benzoateAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of 5-methylpyridin-3-amine (0.5 g, 4.62 mmol) in CH2Cl2 (50 ml) were added triethylamine (0.64 mL, 4.62 mmol) and methyl 2-(chlorosulfonyl)benzoate (1.08 g, 4.62 mmol). The resulting mixture was stirred at room temperature for 1 hour. The mixture was then diluted with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography (0-8% MeOH/CH2Cl2) to give the title compound (0.476 g, 34%). 1H NMR (400 MHz, DMSO-D6) δ ppm 10.25-10.62 (m, 1H) 8.6 (s, 2H) 7.81-7.93 (m, 1H) 7.64-7.76 (m, 2H) 7.54-7.64 (m, 1H) 7.28 (s, 1H) 3.80 (s, 3H) 2.18 (s, 3H).

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography (0-8% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-6f001939915e4bf99a8728db4c5e78d8
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868026B2

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